How to Fall in Love (2012)

An awkward accountant, still grappling with his teenage insecurities, enlists the help of a dating coach—his former high school crush. With her guidance, he successfully attracts a beautiful woman he's admired for ages, only to discover their lack of compatibility. As he navigates his lessons with the coach, lingering feelings from their past resurface. Unbeknownst to him, she shares his feelings, yet he remains paralyzed by the fear of rejection. Torn between his blossoming emotions and his insecurities, he must decide whether to take a chance on love.